It is not known when exactly Jews started to settle in Szczebrzeszyn. However, some researchers indicate even the beginning of the 15th or the end of the 14th centuries. Most probably, the first synagogue in Szczebrzeszyn was built at the beginning of the 16th century. It was devastated during the Chmielnicki Uprising (Khmelnytsky Uprising) when the Cossacks murdered most local Jews.

The 1507 register of Jewish settlements informs that the Jewish kehilla of Szczebrzeszyn paid 25 zlotys of coronation tax,[1.1] which indicates Jews arrived in Szczebrzeszyn before the above mentioned year.

The town owes their arrival probably to a decision of the then owner, Jan Amor Tarnowski. He decided to bring Jews to his estates, as he counted on economic profits. The activity of Jews and the profit it brought indicated that it was a good investment. Jews turned out to be good craftsmen, traders and lessees.[1.2] Among them there were butchers, tailors, carpenters, or woodcarvers[1.3] and later on when merchants appeared in this area, trade became the basic occupation,[1.4] alongside lease[1.5] and grapevine cultivation.[1.6]

The Szczebrzeszyn Jews were cloth, linen and spices traders, and over the years they had developed a kind of specialization, namely, as Maurycy Horn states: colonial food commodities and grain predominated in Szczebrzeszyn (and the nearby town of Turobin).[refr:| M. Horn, Żydzi na Rusi Czerwonej... ]] Jews were spice traders and did their business at Lublin fairs.[1.7]tki Żydów w Ordynacji Zamojskiej, „BŻIH” 1977, nos. 71 – 72. ]]

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